• Libraries
    • Log in to:
    View Item 
    •   MSpace Home
    • Faculty of Graduate Studies (Electronic Theses and Practica)
    • FGS - Electronic Theses and Practica
    • View Item
    •   MSpace Home
    • Faculty of Graduate Studies (Electronic Theses and Practica)
    • FGS - Electronic Theses and Practica
    • View Item
    JavaScript is disabled for your browser. Some features of this site may not work without it.

    A study of a chiral 4-substituted oxazolidin-2-one in asymmetric transformations via soluble polymer-supported synthesis and fluorous synthesis

    Thumbnail
    View/Open
    MQ45124.pdf (9.858Mb)
    Date
    1999-07-01
    Author
    Sudharshan, Manjul
    Metadata
    Show full item record
    Abstract
    Chiral auxiliaries remain one of the most reliable ways of generating new chiral molecules in a highly enantiomerically enriched form. We have synthesized a new chiral -substituted oxazolidin-2-one from ' L'-tyrosine via a novel method. The potential of this methodology has been established. Supporting a chiral auxiliary on a polymer provides a convenient work-up and purification procedure and makes its recovery simple. Careful choice of polymer and auxiliary is essential for its success. The first synthesis of a soluble polymer-supported oxazolidinone from the tyrosine-derived oxazolidin-2-one and the soluble poly(ethylene glycol)-monomethyl ether (MeOPEG) has been described. The behavior of the MeOPEG-supported oxazolidin-2-one in the asymmetric alkylation and the Diels-Alder reaction has been disclosed. Fluorous synthesis introduces an alternative route to traditional and polymer-supported synthesis. The synthesis of a novel, highly fluorinated silyl fluorous tag has been described. The tyrosine-derivedoxazolidin-2-one has been rendered fluorous upon attachment to the fluorous tag. Asymmetric aldol condensation of the fluorous-tagged oxazolidin-2-one has produced all four diastereoisomers and their stereochemical assignments have been confirmed. This is the first demonstration of the suitability of fluorous synthesis strategy for asymmetric synthesis of chiral oxazolidinones.
    URI
    http://hdl.handle.net/1993/1777
    Collections
    • FGS - Electronic Theses and Practica [25494]

    DSpace software copyright © 2002-2016  DuraSpace
    Contact Us | Send Feedback
    Theme by 
    Atmire NV
     

     

    Browse

    All of MSpaceCommunities & CollectionsBy Issue DateAuthorsTitlesSubjectsThis CollectionBy Issue DateAuthorsTitlesSubjects

    My Account

    Login

    Statistics

    View Usage Statistics

    DSpace software copyright © 2002-2016  DuraSpace
    Contact Us | Send Feedback
    Theme by 
    Atmire NV